SK17562000A3 - Furylfosfíny a organokovové komplexy, ktoré ich obsahujú - Google Patents

Furylfosfíny a organokovové komplexy, ktoré ich obsahujú Download PDF

Info

Publication number: SK17562000A3
Authority: SK; Slovakia
Prior art keywords: group; water; complexes; carbon atoms; acids
Prior art date: 1998-05-20

Application number

SK1756-2000A

Other languages

English (en)

Slovak (sk)

Inventor

Francois Mathey

Philippe Savignac

Frédéric Eymery

Paolo Burattin

Original Assignee

Rhodia Fiber And Resin Intermediates

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1998-05-20

Filing date

1999-05-11

Publication date

2001-08-06

1999-05-11 Application filed by Rhodia Fiber And Resin Intermediates filed Critical Rhodia Fiber And Resin Intermediates

2001-08-06 Publication of SK17562000A3 publication Critical patent/SK17562000A3/sk

Links

XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 34
125000002524 organometallic group Chemical group 0.000 claims abstract description 18
238000000034 method Methods 0.000 claims abstract description 11
229910052751 metal Inorganic materials 0.000 claims description 21
239000002184 metal Substances 0.000 claims description 21
239000002253 acid Substances 0.000 claims description 20
125000004432 carbon atom Chemical group C* 0.000 claims description 18
239000000243 solution Substances 0.000 claims description 17
MSBPSFSYBUUPMC-UHFFFAOYSA-N furan-2-ylphosphane Chemical compound PC1=CC=CO1 MSBPSFSYBUUPMC-UHFFFAOYSA-N 0.000 claims description 15
125000000217 alkyl group Chemical group 0.000 claims description 14
238000002360 preparation method Methods 0.000 claims description 14
150000001875 compounds Chemical class 0.000 claims description 13
230000003647 oxidation Effects 0.000 claims description 13
238000007254 oxidation reaction Methods 0.000 claims description 13
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 11
150000007513 acids Chemical class 0.000 claims description 11
-1 alkaline earth metal cations Chemical class 0.000 claims description 11
230000015572 biosynthetic process Effects 0.000 claims description 11
239000010948 rhodium Substances 0.000 claims description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 9
150000002739 metals Chemical class 0.000 claims description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 8
239000002243 precursor Substances 0.000 claims description 8
150000001336 alkenes Chemical class 0.000 claims description 7
125000002091 cationic group Chemical group 0.000 claims description 7
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 6
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
238000011065 in-situ storage Methods 0.000 claims description 6
125000002560 nitrile group Chemical group 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
239000007864 aqueous solution Substances 0.000 claims description 5
150000001768 cations Chemical class 0.000 claims description 5
229910052744 lithium Inorganic materials 0.000 claims description 5
229910052759 nickel Inorganic materials 0.000 claims description 5
229910052707 ruthenium Inorganic materials 0.000 claims description 5
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
150000001449 anionic compounds Chemical group 0.000 claims description 4
125000002541 furyl group Chemical group 0.000 claims description 4
125000001188 haloalkyl group Chemical group 0.000 claims description 4
238000007037 hydroformylation reaction Methods 0.000 claims description 4
238000005984 hydrogenation reaction Methods 0.000 claims description 4
150000002736 metal compounds Chemical class 0.000 claims description 4
150000002815 nickel Chemical class 0.000 claims description 4
150000002891 organic anions Chemical group 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 4
229910052763 palladium Inorganic materials 0.000 claims description 4
229910052697 platinum Inorganic materials 0.000 claims description 4
229910052703 rhodium Inorganic materials 0.000 claims description 4
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 4
150000003303 ruthenium Chemical class 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
239000001569 carbon dioxide Substances 0.000 claims description 3
229910002092 carbon dioxide Inorganic materials 0.000 claims description 3
238000005669 hydrocyanation reaction Methods 0.000 claims description 3
229910052741 iridium Inorganic materials 0.000 claims description 3
GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 3
150000002900 organolithium compounds Chemical class 0.000 claims description 3
229910052762 osmium Inorganic materials 0.000 claims description 3
SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 3
238000003786 synthesis reaction Methods 0.000 claims description 3
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
239000005977 Ethylene Substances 0.000 claims description 2
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
150000001252 acrylic acid derivatives Chemical class 0.000 claims description 2
239000003513 alkali Substances 0.000 claims description 2
229910052783 alkali metal Inorganic materials 0.000 claims description 2
150000001340 alkali metals Chemical class 0.000 claims description 2
238000005865 alkene metathesis reaction Methods 0.000 claims description 2
229910052793 cadmium Inorganic materials 0.000 claims description 2
BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims description 2
229910017052 cobalt Inorganic materials 0.000 claims description 2
239000010941 cobalt Substances 0.000 claims description 2
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 2
229910052802 copper Inorganic materials 0.000 claims description 2
239000010949 copper Substances 0.000 claims description 2
238000006471 dimerization reaction Methods 0.000 claims description 2
125000005610 enamide group Chemical group 0.000 claims description 2
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 2
229910052737 gold Inorganic materials 0.000 claims description 2
239000010931 gold Substances 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
229910001412 inorganic anion Chemical group 0.000 claims description 2
229910052742 iron Inorganic materials 0.000 claims description 2
150000002641 lithium Chemical group 0.000 claims description 2
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 2
229910052753 mercury Inorganic materials 0.000 claims description 2
230000000737 periodic effect Effects 0.000 claims description 2
238000006116 polymerization reaction Methods 0.000 claims description 2
KZVLNAGYSAKYMG-UHFFFAOYSA-N pyridine-2-sulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=N1 KZVLNAGYSAKYMG-UHFFFAOYSA-N 0.000 claims description 2
150000003283 rhodium Chemical class 0.000 claims description 2
229910052709 silver Inorganic materials 0.000 claims description 2
239000004332 silver Substances 0.000 claims description 2
229910052723 transition metal Inorganic materials 0.000 claims description 2
150000003624 transition metals Chemical class 0.000 claims description 2
125000004950 trifluoroalkyl group Chemical group 0.000 claims description 2
229910052725 zinc Inorganic materials 0.000 claims description 2
239000011701 zinc Substances 0.000 claims description 2
150000001299 aldehydes Chemical class 0.000 claims 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 1
150000003871 sulfonates Chemical class 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
239000000203 mixture Substances 0.000 description 24
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
239000003446 ligand Substances 0.000 description 20
238000005481 NMR spectroscopy Methods 0.000 description 19
238000006243 chemical reaction Methods 0.000 description 17
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
239000000047 product Substances 0.000 description 13
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 12
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000002904 solvent Substances 0.000 description 12
229910052757 nitrogen Inorganic materials 0.000 description 11
238000003756 stirring Methods 0.000 description 11
XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
239000002609 medium Substances 0.000 description 8
150000001450 anions Chemical class 0.000 description 7
229910052739 hydrogen Inorganic materials 0.000 description 7
238000010992 reflux Methods 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000012074 organic phase Substances 0.000 description 6
229910000073 phosphorus hydride Inorganic materials 0.000 description 6
WBAXCOMEMKANRN-UHFFFAOYSA-N 2-methylbut-3-enenitrile Chemical compound C=CC(C)C#N WBAXCOMEMKANRN-UHFFFAOYSA-N 0.000 description 5
238000004458 analytical method Methods 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
239000013256 coordination polymer Substances 0.000 description 5
239000012153 distilled water Substances 0.000 description 5
238000001704 evaporation Methods 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
239000007789 gas Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
239000007787 solid Substances 0.000 description 5
UVKXJAUUKPDDNW-NSCUHMNNSA-N (e)-pent-3-enenitrile Chemical compound C\C=C\CC#N UVKXJAUUKPDDNW-NSCUHMNNSA-N 0.000 description 4
CFEYBLWMNFZOPB-UHFFFAOYSA-N Allylacetonitrile Natural products C=CCCC#N CFEYBLWMNFZOPB-UHFFFAOYSA-N 0.000 description 4
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
238000012512 characterization method Methods 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 4
ATHCRLRKGYMSRY-UHFFFAOYSA-N furan-2-yl(diphenyl)phosphane Chemical compound C1=COC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 ATHCRLRKGYMSRY-UHFFFAOYSA-N 0.000 description 4
SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 4
238000006317 isomerization reaction Methods 0.000 description 4
239000012071 phase Substances 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000011734 sodium Substances 0.000 description 4
239000004912 1,5-cyclooctadiene Substances 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
239000012300 argon atmosphere Substances 0.000 description 3
239000002585 base Substances 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000000126 substance Substances 0.000 description 3
101100440699 Drosophila melanogaster corto gene Proteins 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
235000019270 ammonium chloride Nutrition 0.000 description 2
229910052786 argon Inorganic materials 0.000 description 2
230000002051 biphasic effect Effects 0.000 description 2
IYYIVELXUANFED-UHFFFAOYSA-N bromo(trimethyl)silane Chemical compound C[Si](C)(C)Br IYYIVELXUANFED-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
150000001993 dienes Chemical class 0.000 description 2
LGTLXDJOAJDFLR-UHFFFAOYSA-N diethyl chlorophosphate Chemical compound CCOP(Cl)(=O)OCC LGTLXDJOAJDFLR-UHFFFAOYSA-N 0.000 description 2
JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
235000021317 phosphate Nutrition 0.000 description 2
229910052698 phosphorus Inorganic materials 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000000758 substrate Substances 0.000 description 2
238000005406 washing Methods 0.000 description 2
RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 description 1
JRTIUDXYIUKIIE-KZUMESAESA-N (1z,5z)-cycloocta-1,5-diene;nickel Chemical compound [Ni].C\1C\C=C/CC\C=C/1.C\1C\C=C/CC\C=C/1 JRTIUDXYIUKIIE-KZUMESAESA-N 0.000 description 1
POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
MLTKVOFYDBXMDV-UHFFFAOYSA-L C1(=CC=CC=C1)OC(=O)C1=CC=C(O1)PC=1OC(=CC1)C(=O)[O-].[Li+].[Li+].C1(=CC=CC=C1)OC(=O)C1=CC=C(O1)PC=1OC(=CC1)C(=O)[O-] Chemical compound C1(=CC=CC=C1)OC(=O)C1=CC=C(O1)PC=1OC(=CC1)C(=O)[O-].[Li+].[Li+].C1(=CC=CC=C1)OC(=O)C1=CC=C(O1)PC=1OC(=CC1)C(=O)[O-] MLTKVOFYDBXMDV-UHFFFAOYSA-L 0.000 description 1
LZCLECGMZWYEAJ-UHFFFAOYSA-L C1(=CC=CC=C1)OS(=O)C1=CC=C(O1)PC=1OC(=CC1)S(=O)[O-].[Li+].[Li+].C1(=CC=CC=C1)OS(=O)C1=CC=C(O1)PC=1OC(=CC1)S(=O)[O-] Chemical compound C1(=CC=CC=C1)OS(=O)C1=CC=C(O1)PC=1OC(=CC1)S(=O)[O-].[Li+].[Li+].C1(=CC=CC=C1)OS(=O)C1=CC=C(O1)PC=1OC(=CC1)S(=O)[O-] LZCLECGMZWYEAJ-UHFFFAOYSA-L 0.000 description 1
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
241000723347 Cinnamomum Species 0.000 description 1
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
KBEBGUQPQBELIU-CMDGGOBGSA-N Ethyl cinnamate Chemical compound CCOC(=O)\C=C\C1=CC=CC=C1 KBEBGUQPQBELIU-CMDGGOBGSA-N 0.000 description 1
238000007341 Heck reaction Methods 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
238000006069 Suzuki reaction reaction Methods 0.000 description 1
229920006362 Teflon® Polymers 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
ZAENXHXQWSDUOG-UHFFFAOYSA-N benzene;iodine Chemical compound [I].C1=CC=CC=C1 ZAENXHXQWSDUOG-UHFFFAOYSA-N 0.000 description 1
RVYNMHOCCBZORR-UHFFFAOYSA-N bis(furan-2-yl)-phenylphosphane Chemical compound C1=COC(P(C=2OC=CC=2)C=2C=CC=CC=2)=C1 RVYNMHOCCBZORR-UHFFFAOYSA-N 0.000 description 1
CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
229910002091 carbon monoxide Inorganic materials 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
KBEBGUQPQBELIU-UHFFFAOYSA-N cinnamic acid ethyl ester Natural products CCOC(=O)C=CC1=CC=CC=C1 KBEBGUQPQBELIU-UHFFFAOYSA-N 0.000 description 1
235000017803 cinnamon Nutrition 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000010668 complexation reaction Methods 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
238000007872 degassing Methods 0.000 description 1
208000002925 dental caries Diseases 0.000 description 1
IMDXZWRLUZPMDH-UHFFFAOYSA-N dichlorophenylphosphine Chemical compound ClP(Cl)C1=CC=CC=C1 IMDXZWRLUZPMDH-UHFFFAOYSA-N 0.000 description 1
239000000539 dimer Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000003480 eluent Substances 0.000 description 1
DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000003760 magnetic stirring Methods 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000012544 monitoring process Methods 0.000 description 1
239000000178 monomer Substances 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
150000002940 palladium Chemical class 0.000 description 1
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
229920002545 silicone oil Polymers 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
UWJPVZQCWNKCID-UHFFFAOYSA-K tetrasodium phenoxy-[5-(5-phosphonatofuran-2-yl)phosphanylfuran-2-yl]phosphinate Chemical compound C1(=CC=CC=C1)OP([O-])(=O)C1=CC=C(O1)PC=1OC(=CC=1)P([O-])(=O)[O-].[Na+].[Na+].[Na+].[Na+] UWJPVZQCWNKCID-UHFFFAOYSA-K 0.000 description 1
230000007704 transition Effects 0.000 description 1
DLQYXUGCCKQSRJ-UHFFFAOYSA-N tris(furan-2-yl)phosphane Chemical compound C1=COC(P(C=2OC=CC=2)C=2OC=CC=2)=C1 DLQYXUGCCKQSRJ-UHFFFAOYSA-N 0.000 description 1
SOBHUZYZLFQYFK-UHFFFAOYSA-K trisodium;hydroxy-[[phosphonatomethyl(phosphonomethyl)amino]methyl]phosphinate Chemical compound [Na+].[Na+].[Na+].OP(O)(=O)CN(CP(O)([O-])=O)CP([O-])([O-])=O SOBHUZYZLFQYFK-UHFFFAOYSA-K 0.000 description 1
238000001665 trituration Methods 0.000 description 1
238000013022 venting Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0073—Rhodium compounds
- C07F15/008—Rhodium compounds without a metal-carbon linkage
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/14—Preparation of carboxylic acid amides by formation of carboxamide groups together with reactions not involving the carboxamide groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/65515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

SK1756-2000A 1998-05-20 1999-05-11 Furylfosfíny a organokovové komplexy, ktoré ich obsahujú SK17562000A3 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR9806559A FR2778915B1 (fr)	1998-05-20	1998-05-20	Nouvelles furylphosphines et complexes organometalliques les comprenant
PCT/FR1999/001129 WO1999060003A1 (fr)	1998-05-20	1999-05-11	Nouvelles furylphosphines et complexes organometalliques les comprenant

Publications (1)

Publication Number	Publication Date
SK17562000A3 true SK17562000A3 (sk)	2001-08-06

Family

ID=9526678

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1756-2000A SK17562000A3 (sk)	1998-05-20	1999-05-11	Furylfosfíny a organokovové komplexy, ktoré ich obsahujú

Country Status (18)

Country	Link
US (1)	US6417375B1 (fr)
EP (1)	EP1080096B1 (fr)
JP (1)	JP2002515506A (fr)
KR (1)	KR100404157B1 (fr)
CN (1)	CN1152035C (fr)
BR (1)	BR9910627A (fr)
CA (1)	CA2333183A1 (fr)
CZ (1)	CZ20004300A3 (fr)
DE (1)	DE69906722T2 (fr)
ES (1)	ES2192047T3 (fr)
FR (1)	FR2778915B1 (fr)
PL (1)	PL344285A1 (fr)
RU (1)	RU2198891C2 (fr)
SK (1)	SK17562000A3 (fr)
TW (1)	TW568916B (fr)
UA (1)	UA66851C2 (fr)
WO (1)	WO1999060003A1 (fr)
ZA (1)	ZA200006725B (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2819250B1 (fr) *	2001-01-05	2004-12-03	Rhodia Polyamide Intermediates	Procede de fabrication de composes nitriles a partir de composes a insaturation ethylenique
FR2932476B1 (fr) *	2008-06-17	2010-07-30	Rhodia Operations	Procede de fabrication de composes nitriles a partir de composes a insaturation ethylenique
FR2932477B1 (fr) *	2008-06-17	2013-01-18	Rhodia Operations	Procede de fabrication de composes nitriles a partir de composes a insaturation ethylenique
CN103012480B (zh) *	2012-12-27	2016-01-20	北京格林凯默科技有限公司	一种三(2-呋喃基)膦的制备方法
CN114669294A (zh) *	2022-04-13	2022-06-28	宏业生物科技股份有限公司	2,2-二(2-呋喃基)丙烷加氢制2,2-二(2-四氢呋喃基)丙烷的复合催化剂

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2314910A1 (fr) *	1975-06-20	1977-01-14	Rhone Poulenc Ind	Procede d'hydroformylation des olefines
US4880902A (en) *	1987-08-27	1989-11-14	Shell Oil Company	Copolymerization of carbon monoxide and olefin with diphosphine having heterocyclic substituents as catalyst
NL9001114A (nl) *	1990-05-10	1991-12-02	Shell Int Research	Katalysatorcomposities.
US5739396A (en) *	1991-12-09	1998-04-14	Stanford University	Asymmetric ligands useful for transition metal catalyzed bond forming reactions
IT1270082B (it) *	1994-07-12	1997-04-28	Univ Degli Studi Milano	Difosfine eteroaromatiche come leganti chirali, complessi tra dette difosfine e metalli di transizione ed impiego di detti complessi come catalizzatori chirali
IT1286497B1 (it) *	1996-11-20	1998-07-15	Italfarmaco Sud Spa	Difosfine di tipo misto eteroariliche-ariliche come leganti chirali, relativi complessi con metalli di transizione e impiego di detti

1998
- 1998-05-20 FR FR9806559A patent/FR2778915B1/fr not_active Expired - Fee Related
1999
- 1999-05-11 CN CNB99807666XA patent/CN1152035C/zh not_active Expired - Fee Related
- 1999-05-11 CZ CZ20004300A patent/CZ20004300A3/cs unknown
- 1999-05-11 WO PCT/FR1999/001129 patent/WO1999060003A1/fr not_active Ceased
- 1999-05-11 PL PL99344285A patent/PL344285A1/xx not_active IP Right Cessation
- 1999-05-11 US US09/700,750 patent/US6417375B1/en not_active Expired - Fee Related
- 1999-05-11 DE DE69906722T patent/DE69906722T2/de not_active Expired - Fee Related
- 1999-05-11 RU RU2000132220/04A patent/RU2198891C2/ru not_active IP Right Cessation
- 1999-05-11 SK SK1756-2000A patent/SK17562000A3/sk unknown
- 1999-05-11 JP JP2000549621A patent/JP2002515506A/ja active Pending
- 1999-05-11 CA CA002333183A patent/CA2333183A1/fr not_active Abandoned
- 1999-05-11 KR KR10-2000-7013043A patent/KR100404157B1/ko not_active Expired - Fee Related
- 1999-05-11 UA UA2000116541A patent/UA66851C2/uk unknown
- 1999-05-11 EP EP99918056A patent/EP1080096B1/fr not_active Expired - Lifetime
- 1999-05-11 BR BR9910627-2A patent/BR9910627A/pt not_active IP Right Cessation
- 1999-05-11 ES ES99918056T patent/ES2192047T3/es not_active Expired - Lifetime
- 1999-05-18 TW TW088108102A patent/TW568916B/zh not_active IP Right Cessation
2000
- 2000-11-17 ZA ZA200006725A patent/ZA200006725B/xx unknown

Also Published As

Publication number	Publication date
US6417375B1 (en)	2002-07-09
CN1306537A (zh)	2001-08-01
FR2778915A1 (fr)	1999-11-26
ZA200006725B (en)	2002-01-21
DE69906722D1 (de)	2003-05-15
RU2198891C2 (ru)	2003-02-20
ES2192047T3 (es)	2003-09-16
EP1080096A1 (fr)	2001-03-07
WO1999060003A1 (fr)	1999-11-25
CN1152035C (zh)	2004-06-02
PL344285A1 (en)	2001-10-22
BR9910627A (pt)	2001-01-30
FR2778915B1 (fr)	2000-06-30
UA66851C2 (uk)	2004-06-15
TW568916B (en)	2004-01-01
KR100404157B1 (ko)	2003-11-01
EP1080096B1 (fr)	2003-04-09
JP2002515506A (ja)	2002-05-28
KR20010103550A (ko)	2001-11-23
DE69906722T2 (de)	2004-02-05
CZ20004300A3 (cs)	2001-09-12
CA2333183A1 (fr)	1999-11-25

Publication	Publication Date	Title
CA2380626C (fr)	2009-12-15	Hydroformylation utilisant des ligands a phosphites multidentes
KR100450102B1 (ko)	2004-09-24	양이온성 복소환식 카르벤을 포함하는 유기금속 착체
JP2004513950A (ja)	2004-05-13	オルト置換キラルホスフィンおよびホスフィナイトならびに非対称触媒反応でのその使用
JP2003522162A (ja)	2003-07-22	キラルフェロセンホスフィン及び不斉触媒反応におけるその使用
WO2004076464A2 (fr)	2004-09-10	Phosphites et phosphoramidites optiquement actifs et dotes d'un squelette biphenol a chiralite axiale, leur utilisation dans des reactions catalytiques asymetriques
JP4342942B2 (ja)	2009-10-14	新規ジホスフィン、遷移金属との錯体、及び、不斉合成での使用
EP0826691A2 (fr)	1998-03-04	Composés diphosphines optiquement actives, procédé de leur préparation, complexes de métal de transition contenant ces composés comme ligand et procédé de préparation de substances optiquement actives par utilisation de ces complexes
SK17562000A3 (sk)	2001-08-06	Furylfosfíny a organokovové komplexy, ktoré ich obsahujú
EP1095946B1 (fr)	2003-08-27	Composé diphosphine d'activité optique, composés intermédiaires de préparation, complexe métal de transition le contenant comme ligand et catalysateur pour des hydrogénations asymmétriques contenant le complexe
EP0839819B1 (fr)	2003-09-17	Procédé de préparation de ligands diphosphine optiquement actifs
US7009065B2 (en)	2006-03-07	Ferrocenyl ligands and the use thereof in catalysis
CA2597883A1 (fr)	2006-08-24	Catalyseur pour synthese asymetrique, ligand pour une utilisation dans celui-ci, et procede destine a produire un compose optiquement actif a travers une reaction de synthese asymetrique les utilisant
MXPA00011325A (en)	2001-12-04	Novel furylphosphines and organometallic complexes containing them
Johnson et al.	2022	Simplified Synthesis of Air-stable Copper-complexed Josiphos Ligand via Ugi’s Amine: Complete Preparation and Analysis from Ferrocene
RU2556224C1 (ru)	2015-07-10	Способ получения катионных комплексов палладия с дииминовыми лигандами
KR20250177362A (ko)	2025-12-23	2-페닐페놀 외부 단위를 갖는 비스포스파이트
Li	2009	Extending the Phosphorus-donor Manifold from Symmetric to Unsymmetric in Pincer Metal Catalysts